The Edit

Eight Shoes Every Man Should Own

Brogues, Oxfords and Chelsea boots are just some of the building blocks in a proper wardrobe

Words by Mr John Brodie, Editorial Director US, MR PORTER

Just as Batman needs batarangs, smoke pellets and a grapple gun to get through the daily grind of beating up bad guys, a man of style should have an arsenal of proper shoes to take him through his week, whatever it may involve. Think of them as items for your sartorial utility belt. The styles should a) veer from formal (Oxfords) to casual (driving moccasins); b) come in different materials, and shades of leather; c) hail from a variety of shoemakers and d) have soles that are appropriate for all weather conditions. We do not view the list below as exhaustive, merely an elegant foundation. If properly cared for, it is not uncommon for the hard-soled shoes on this list to last 15 years, so we have erred on the side of timelessness when it comes to the styles selected.

It used to be that clean, cap-toe black Oxfords (such as these by John Lobb), were the first shoes a man would sink his capital into. This advice dates back to an era when the dress code in most offices was a suit. Still, for weddings, funerals and that day when the CEO finally notices you, these are the stately companions of that type of dark suit. The term “cap toe” refers to the line of stitching bisecting the toe. The only workplace shoes that are dressier would be whole-cut Oxfords, a completely unadorned shoe made from one single piece of leather, hence the name “whole cut” or “one cut”.

If you want to buy boots that work in bad weather, you go to a bootmaker from Red Wing, Minnesota. Red Wing isn’t exactly the North Country immortalised in Mr Bob Dylan’s lyrics, but it is a place where winds hit heavy, snowflakes storm and rivers freeze. Stitched and rubber-soled for durability, these are not a designer’s idea of workwear. Rather, they are the sort of boots that people who actually work outside wear. Their authenticity of origin and purpose make them the perfect shoes to wear with jeans, or on days when the weather can only be described as terrible.

Just like shortbread, whisky (well, at least the kind without the “e”) and Sir Sean Connery, brogues are a Scottish creation that have proved popular the world over. The term “brogue” is more about the decoration on a shoe rather than its cut, referring to the way that the surface is punctured and stitched to form a pattern. Originally developed for outdoor use, the distinctive perforations were designed to allow water to drain out of the shoes. Wing tips, such as these from George Cleverley, are a flash member of the brogue family, thanks to a decorative detail on the toe. Cleverley was the shoemaker of choice for Sir Winston Churchill and Mr Charlie Watts. And like the latter’s drum backbeat, these are quietly powerful, yet have a jazzy flair.

Leather boots held together by elastic bands were initially patented by bootmaker Mr J Sparkes-Hall as a walking shoe for Queen Victoria. Like their cousin, jodhpurs, Mr Sparkes-Hall’s boots became a favourite of the equestrian set and only acquired the “Chelsea” moniker in the Swinging Sixties when that part of London was ground zero for mods. Since then, a number of designers – most notably Gucci, Maison Margiela and Saint Laurent – have created beautiful variations of Chelsea boots with vintage rock ’n’ roll swagger. For those looking for a more classic and affordable model, we like R.M.Williams. Based in Adelaide, the Australian firm, which dates back to 1932, got its start designing boots for cowboys in the outback. If you’re in the market for two pairs, might we suggest getting one in leather and the other in suede?

Initially created as a walking shoe for country gentlemen, Derbies have become one of the most versatile shoes a man can own. They can dress up a pair of jeans, but they can also add a bit of devil-may-care to a suit. Derbies, which are less formal than Oxfords, are distinguished by the fact that the facing (where the lace eyelets are located) is open at the bottom, while Oxfords' facing is closed, presenting a smoother façade to the world. We are partial to Derbies with a rubber sole, so it can become the go-to dress shoe on a rainy day. Edward Green is one of several Northampton shoemakers that makes this British town world-renowned for its craftsmanship.

Like email or smartphones, driving moccasins are one of those 1990s inventions that modern man never knew he needed, yet now can’t imagine his life without. While Tod's CEO Mr Diego Della Valle may not have invented car shoes, his leather moccasins with rubber "pebbles" in the sole became the catalyst for the exponential growth that transformed a family-run leather goods business dating back to the 1920s into a global brand. Even if you are chasing after your dog on its walkies rather than accelerating through a switchback turn on the Amalfi Coast, these comfortable and classic shoes are a slightly more stylish alternative to boat shoes and more versatile than sandals.

Handcrafted in Limoges, France, with leather from its own tannery, J.M. Weston 180 Moccasins are still designed to the same spec as when they debuted in 1946. While other penny loafers, including Bass Weejuns, became icons of collegiate cool in the US, J.M. Weston loafers appeared on the feet of both the establishment (French presidents Messrs François Mitterrand and Jacques Chirac were fans) and the rebellious: see La Bande du Drugstore in which a 1960s post-beatnik Parisian tribe hang out sans socks in their Westons. They were bourgeois youths who appropriated trends from their parents while attempting to mock them. Here at MR PORTER, we like our parents and we like these loafers in either burgundy or black. NB They come up half a size too small, so be sure to check the measurements.

These double monk straps are perfect for those occasions when the dress code calls for a suit, but you want to emit a low dog whistle that shows you are not another corporate drone and are, in fact, a closet libertine ready to give your corporate card a spanking at a moment’s notice. Like outboard motors and shotguns, some men prefer singles, others a double. These are a classic double friar in a black pebble-grain leather, finished with a toe-cap construction and stitch-seam detail.